VDN

2-{2-ETHOXY-5-[(4-ETHYLPIPERAZIN-1-YL)SULFONYL]PHENYL}-5-METHYL-7-PROPYLIMIDAZO[5,1-F][1,2,4]TRIAZIN-4(1H)-ONE

Created: 2003-07-10
Last modified:  2020-06-05

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Chemical Details

Formal Charge0
Atom Count66
Chiral Atom Count0
Bond Count69
Aromatic Bond Count17
2D diagram of VDN

Chemical Component Summary

Name2-{2-ETHOXY-5-[(4-ETHYLPIPERAZIN-1-YL)SULFONYL]PHENYL}-5-METHYL-7-PROPYLIMIDAZO[5,1-F][1,2,4]TRIAZIN-4(1H)-ONE
SynonymsVARDENAFIL, LEVITRA
Systematic Name (OpenEye OEToolkits)2-[2-ethoxy-5-(4-ethylpiperazin-1-yl)sulfonyl-phenyl]-5-methyl-7-propyl-1H-imidazo[5,1-f][1,2,4]triazin-4-one
FormulaC23 H32 N6 O4 S
Molecular Weight488.603
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs10.04O=C2N=C(Nn1c(nc(c12)C)CCC)c3cc(ccc3OCC)S(=O)(=O)N4CCN(CC)CC4
SMILESCACTVS3.341CCCc1nc(C)c2n1NC(=NC2=O)c3cc(ccc3OCC)[S](=O)(=O)N4CCN(CC)CC4
SMILESOpenEye OEToolkits1.5.0CCCc1nc(c2n1NC(=NC2=O)c3cc(ccc3OCC)S(=O)(=O)N4CCN(CC4)CC)C
Canonical SMILESCACTVS3.341 CCCc1nc(C)c2n1NC(=NC2=O)c3cc(ccc3OCC)[S](=O)(=O)N4CCN(CC)CC4
Canonical SMILESOpenEye OEToolkits1.5.0 CCCc1nc(c2n1NC(=NC2=O)c3cc(ccc3OCC)S(=O)(=O)N4CCN(CC4)CC)C
InChIInChI1.03 InChI=1S/C23H32N6O4S/c1-5-8-20-24-16(4)21-23(30)25-22(26-29(20)21)18-15-17(9-10-19(18)33-7-3)34(31,32)28-13-11-27(6-2)12-14-28/h9-10,15H,5-8,11-14H2,1-4H3,(H,25,26,30)
InChIKeyInChI1.03 SECKRCOLJRRGGV-UHFFFAOYSA-N

Drug Info: DrugBank

DrugBank IDDB00862 
NameVardenafil
Groups approved
DescriptionVardenafil is a selective inhibitor of cyclic guanosine monophosphate (cGMP)-specific phosphodiesterase type 5 (PDE5) and an oral therapy for the treatment of erectile dysfunction.[L45563,L45568] During sexual stimulation, nitric oxide (NO) is released from nerve endings and endothelial cells in the corpus cavernosum, activating the enzyme guanylate cyclase and increasing the synthesis of cGMP in the smooth muscle cells of the corpus cavernosum. PDE5 inhibitors, such as vardenafil, inhibit the degradation of cGMP and allow increased blood flow into the penis, resulting in an erection.[A258303,L45563,L45568]. Compared to [sildenafil] and [tadalafil], vardenafil is a more potent inhibitor of PDE5; however, its selectivity for other PDE isoforms is lower than the one detected for tadalafil.[A258318] The FDA approved the use of vardenafil for the treatment of erectile dysfunction in 2003. Although other PDE5 inhibitors such as [sildenafil] and [tadalafil] have been associated with rare cases of acute liver injury, the use of vardenafil has not been linked to hepatotoxic effects.[A258313] The use of vardenafil as a monotherapy for the treatment of pulmonary arterial hypertension has also been evaluated.[A258308]
Synonyms
  • Vardenafilo
  • Vardenafil
  • Vardénafil
  • Vardenafilum
  • Vardenafil hydrochloride
Brand Names
  • Ag-vardenafil
  • Apo-vardenafil
  • Vardenafil hydrochloride
  • Staxyn
  • Jamp-vardenafil ODT
IndicationVardenafil is indicated for the treatment of erectile dysfunction.[L45563,L45568,L45573]
Categories
  • Cardiovascular Agents
  • Cytochrome P-450 CYP2C19 Inhibitors
  • Cytochrome P-450 CYP2C19 Inhibitors (weak)
  • Cytochrome P-450 CYP2C8 Inhibitors
  • Cytochrome P-450 CYP2C8 Inhibitors (weak)
ATC-CodeG04BE09
CAS number224785-90-4

Drug Targets

NameTarget SequencePharmacological ActionActions
cGMP-specific 3',5'-cyclic phosphodiesteraseMERAGPSFGQQRQQQQPQQQKQQQRDQDSVEAWLDDHWDFTFSYFVRKAT...unknowninhibitor
Retinal rod rhodopsin-sensitive cGMP 3',5'-cyclic phosphodiesterase subunit gammaMNLEPPKAEFRSATRVAGGPVTPRKGPPKFKQRQTRQFKSKPPKKGVQGF...unknowninhibitor,allosteric modulator
Retinal cone rhodopsin-sensitive cGMP 3',5'-cyclic phosphodiesterase subunit gammaMSDNTTLPAPASNQGPTTPRKGPPKFKQRQTRQFKSKPPKKGVKGFGDDI...unknowninhibitor,allosteric modulator
Cytochrome P450 3A4MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...unknownsubstrate,inhibitor
Cytochrome P450 3A5MDLIPNLAVETWLLLAVSLVLLYLYGTRTHGLFKRLGIPGPTPLPLLGNV...unknownsubstrate
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL1520
PubChem 135400189, 110634
ChEMBL CHEMBL1520
ChEBI CHEBI:46295
CCDC/CSD ULATOT